Arezzo and Cortona Italy

I will be going in mid September. I see very little about Cortona when I google best places to see in Tuscany. I guess I am wondering if anyone has been and would recommend going.

Cortona is the town made famous most recently by the "Under the Tuscan Sun" author Frances Mayes so it is very much discovered. Cortona is also routinely voted one of the most beautiful Tuscan hilltown villages which is no mean feat given how charming they can be. The town is a true hilltown built essentially on a slant running uphill from the start of town.
The Cortona train station - Camucia-Cortona - is actually at the bottom of the hill and you will need to connect to a bus to get up to the actual hilltown.

Arezzo is an interesting mix of smaller old town on the top of the hill and newer flat town - where the train station is - blending into the older section as you run uphill. If it is steep your in the old section. It has some churches and some very old sections (the roots are Etruscan) and park at the top of hill. Arezzo's population is 4-5x that of Cortona so they are different kinds of towns.

As alluded to by another poster could easily fill a whole day by itself so it depends on how much of it you want to see before moving on. Either one is probably a good day trip both is probably a whirlwind flying visit to both but is doable in a long day.
You're probably an hour or so from Florence to Arezzo and the 20 minutes onto Cortona plus the bus coordination up to the town. And then the bus down and 1.5 hours or so back to Florence. So you're probably looking at 3-4 hours spent on transportation on top of whatever sight seeing you want to do.

If this sounds like what you're looking for then it is entirely do-able.

Have a great trip whatever you decide to do,
=Tod

We loved Cortona, especially in the evening when lots of locals came out to stroll (La Passeggiata) and sit in the main square to visit. My husband sat on a bench with a bunch of local men. We stayed three nights and used it as a base to visit Tuscany. The best gelato I had was in Cortona, and we tried gelato in practically every town we visited. I also appreciated the escalators up to this hill town while wearing my backpack.

It is doable, but it is going to be a long day, and of course you will need to be selective on the things you want to see.